Sodium Hydroxide → Benzyl 4-tert-butoxycarbonylmethoxy-[1,4']bipiperidinyl-1'-carboxylate

HRID 2267230Notes

Reaction equation

HRID 2267230 reaction equation
C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].O=[C:16]1[CH2:21][CH2:20][N:19]([C:22]([O:24][CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)=[O:23])[CH2:18][CH2:17]1.[NH:32]1[CH2:37][CH2:36][CH:35]([O:38][CH2:39][C:40]([O:42][C:43]([CH3:46])([CH3:45])[CH3:44])=[O:41])[CH2:34][CH2:33]1.[OH-].[Na+]>C1COCC1.CCOC(C)=O>[C:43]([O:42][C:40]([CH2:39][O:38][CH:35]1[CH2:34][CH2:33][N:32]([CH:16]2[CH2:21][CH2:20][N:19]([C:22]([O:24][CH2:25][C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)=[O:23])[CH2:18][CH2:17]2)[CH2:37][CH2:36]1)=[O:41])([CH3:46])([CH3:44])[CH3:45]

Participants

7

Reactant 4

HCID 14798Sodium HydroxideHCID 643496Benzyl 4-oxopiperidine-1-carboxylateHCID 5049666Sodium triacetoxyborohydrideHCID 10036224Tert-butyl (piperidin-4-yloxy)-acetate

Product 1

HCID 66941898Benzyl 4-tert-butoxycarbonylmethoxy-[1,4']bipiperidinyl-1'-carboxylate

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

2.90 g (13.27 mmol) sodium triacetoxyborohydride were added batchwise to a mixture of 2.58 g (11.06 mmol) benzyl 4-oxo-piperidine-1-carboxylate and 2.80 g (12.36 mmol) tert-butyl (piperidin-4-yloxy)-acetate in 30 mL THF and the reaction mixture was stirred overnight at RT. It was combined with 50 mL 1 M NaOH, the mixture was stirred for 1 h at RT, combined with EtOAc, the organic phase was separated off and dried over Na2SO4. After elimination of the desiccant and solvent the residue was purified by chromatography (Alox, DCM/MeOH 100:1).

Workup

  1. stirringthe mixture was stirred for 1 h at RT
  2. customthe organic phase was separated off
  3. dry with materialdried over Na2SO4
  4. customAfter elimination of the desiccant and solvent the residue was purified by chromatography (Alox, DCM/MeOH 100:1)

Sources & evidence

ORD record
ord-37ca8846d6404beda73098654e29f503
Source dataset
uspto-grants-2010_12
Patent number
US07858622B2

Reaction notes

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